Live from KICK. START. SMART: The 4 Road Blocks Every Entrepreneur Will Inevitably Come up Against

And how to keep your foot on the accelerator.


So, you’ve decided to start a business. You’ve got your idea (or the major part of it, at least), a great idea for an Instagram page (you’ve already secured the handle!) and even printed out some swank business cards. Hooray!

Good: keep that enthusiasm. You’re going to need it. If there’s anything we learnt from the morning session at our very own Kick. Start. Smart event in Sydney, it’s that building booming business is about 10% good idea and 90% good, old fashioned hard work (or thereabouts).

And our introductory guests – Stevan Premutico, founder of disruptive restaurant booking site Dimmi, Head of Public Affairs at the inimitable Airbnb, Dylan Smith, founder of the multi-city fitness studio Barre Body Emma Seibold and CMO of accounting software superstar Xero Andy Lark – would know. If there’s anyone we can best learn from, it would be those who’ve tread the path before.

Here are a few stop signs you’ll spot on your journey as an entrepreneur – and a few ways you can learn to drive on through.


Rejection (after rejection, after rejection).

This early stage of business building is more of a hurdles race than a single roadblock, if the success story of Stevan’s journey is anything to go by.

After knowing in his gut that he wanted to “make a dent” in the world with a killer business idea, Stevan gave up his top-dog job at Hilton Hotels to build Dimmi, the restaurant reservations site that he’s since successfully sold to TripAdvisor.

Discussing the state of start-ups, Stevan was anything but forgiving. Explaining that while some think the idea of starting your own business looks “cool” and “exciting”, Stevan sets the record straight.

“The truth be told – start-ups are anything but,” he told today’s crowd. “We’re not meant to make it through. Everything is stacked against us.”

For Stevan, it took a perfectly brutal 37 rejections before a door was finally opened when it came to funding his venture. What kept him pushing though, was a gut feeling that what he wanted to do was really worth the effort.


Daily doubts.

Whether it’s one or one hundred rejections you encounter in the early stages, that sneaky sense of self-doubt will inevitably become an unwelcome visitor. For Barre Body’s Emma Seibold, overcoming the often debilitating threat of failure meant holding fast to the idea that throwing everything she had into a business and losing it wasn’t really the end of the world.

“What’s the worst that can happen?” Emma recounts of some sound advice. Realising that for her, the worst outcome was having to give the idea up and go back to a ‘normal’ job, wasn’t reason enough not to follow her passion.

As Airbnb’s Dylan also helpfully explained to the crowd, it matters more that 100 people love your idea over 1000 people are lukewarm about it.

Focus on the small, minuscule wins to help keep the faith.


Opposition to your ideas.

Airbnb may be the powerhouse you know now but for every new disruption, comes a host of status quo straddlers that can’t even imagine your vision, let alone put their money, time or effort into it. As Dylan told out audiences, the team at Airbnb worked tirelessly to overcome opposition to their product. ‘Who would want to stay in a stranger’s home? What if something gets damanged?’ Tackling this criticism head on was their tactic, Dylan dubbing it: ‘leaning into the uncomfortable truth’ of your product. Don’t hide from potential hurdles: call out the opposition and counter it.

Xero’s Andy also pointed out, the very basis of your success will depend on how much you challenge the things around you. So make like Sheryl Sandberg and lean in.



For Stevan, the (very) early days of business meant giving up his “lush CBD office” to work from his garage at my Mum’s house and paid himself nothing for three years. For Emma, it meant halting ten years of hard work in marketing to pursue something different. Andy even let us in on the very first day of Xero – a single book strewn desk barely collecting any natural light: these tough times are the very first step on a much larger, longer journey.

You might start work out of your garage and hand write business cards: but, Emma’s parting sentiment echoed throughout the auditorium: just get started. It’s time.

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